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The document presents a series of organic chemistry problems involving the identification of various organic compounds based on their molecular formulas and reactions. Each problem requires deducing the structures of compounds A, B, C, D, and E, along with the relevant chemical reactions. The problems cover a range of topics including reactions with reagents like Tollen's reagent, Cannizzaro reaction, and oxidation processes.

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6 views

org story questions

The document presents a series of organic chemistry problems involving the identification of various organic compounds based on their molecular formulas and reactions. Each problem requires deducing the structures of compounds A, B, C, D, and E, along with the relevant chemical reactions. The problems cover a range of topics including reactions with reagents like Tollen's reagent, Cannizzaro reaction, and oxidation processes.

Uploaded by

subliminal7777777
Copyright
© © All Rights Reserved
We take content rights seriously. If you suspect this is your content, claim it here.
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Download as PDF, TXT or read online on Scribd
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Class 12-ORGANIC STORY PROBLEMS

1. An organic compound ‘A’ C8H6 on treatment with dilute H2SO4 containing mercuric
sulphate gives compound ‘B’. This compound ‘B’ can also be obtained from a reaction of
benzene with acetyl chloride in presence of anhyd AlCl3. ‘B’ on treatment with I2 in aq.
KOH gives ‘C’ and a yellow compound ‘D’. Identify A, B, C and D. Give the chemical
reactions involved.

2. An organic compound with the molecular formula C7H6O forms 2,4-DNP derivative,
reduces Tollen’s reagent and undergoes Cannizzaro reaction. On oxidation, it gives
benzoic acid. Identify the compound and state the reactions involved.

3. An organic compound A’ with molecular formula C 7H 7NO reacts with Br2/aqKOH to


give compound B’, which upon reaction with NaNO 2& HCl at O°C gives C’. Compound
C’ on heating with CH 3CH 2OH gives a hydrocarbon D’. Compound B’ on further
reaction with Br2 water gives white precipitate of compound E’. Identify the compound
A, B, C, D&E; also justify your answer by giving relevant chemical equations.

4. An Alkyl halide X, of formula C6H13Cl on treatment with potassium tertiary butoxide


gives isomeric alkenes Y and Z(C6H12). Both alkenes on hydrogenation
give 2,3-dimethylbutane. Predict the structures of X, Y and Z.

5. A compound A (C4H10O) is found to be soluble in concentrated sulphuric acid.(A) does


not react with sodium metal or potassium permanganate. When (A) is heated with excess
of HI, it gives a single alkyl halide. Deduce the structure of compound (A) and its IUPAC
name and explain its reaction involved with HI.

6. An organic compound (A) on treatment with CHCl3 and KOH gives two compounds B
and C. Both B and C give the same product (D) when distilled with zinc dust. Oxidation
of D gives E having molecular formula C7H6O2. The sodium salt of E on heating with
soda-lime gives F which may also be obtained by distilling A with zinc dust. Identify A to
F
7. Etherial solution of an organic compound 'A' when heated with magnesium gave 'B'. 'B'
on treatment with ethanal followed by acid hydrolysis gave 2-propanol. Identify the
compound 'A'and B.What is 'B' known as?

8. An alcohol A (C4H10O) on oxidation with acidified potassium dichromate gives


carboxylic acid B(C4H8O2). Compound A when dehydrated with conc. H2SO4 at 443 K
gives compound C. Treatment of C with aqueous H2SO4 gives compound D. (C 4H10O)
which is an isomer of A. Compound D is resistant to oxidation but compound A can be
easily oxidized. Identify A, B, C and D and write their structures. Name the isomerism
present in A and D.

9. An organic compound A having molecular formula C6H6O gives a characteristic colour


with aqueous FeCl3. When A is treated with NaOH and CO2 at 400 K under pressure
compound B is obtained. Compound B on acidification gives, compound C which reacts
with acetyl chloride to form D, which is a popular pain killer. Deduce the structure of A,
B, C and D. What is the popular name of Drug D?

10. An ether A (C5H12O) when heated with excess of hot concentrated HI produced two alkyl
halides which on hydrolysis from compounds B and C. Oxidation of B gives an acid D
whereas oxidation of C gave a ketone E. Deduce the structures of A, B, C, D and E.

11. An organic compound A, C6H10 O, on reaction with MgBr and hydrolysis form an alcohol
followed by acid treatment gives compound B. The compound B on ozonolysis gives
compound C, which in presence of a base gives 1 – acetyl cyclopentene, D. The
compound B on reaction with HBr gives compound E. Write the structures of A, B, C, D
and E. Show how D is formed from C.

12. An organic compound A contains 69.77% carbon, 11.63% hydrogen and rest oxygen. The
molecular mass of the compound is 86. It does not reduce Tollen’s reagent but forms an
addition compound with sodium hydrogen sulphite and gives positive iodoform test. On
vigorous oxidation it gives ethanoic and propanoic acids. Derive the possible
structure of compound A.
13. An organic compound (A) (molecular formula C8H16O2) was hydrolysed with dilute
sulphuric acid to give a carboxylic acid (B) and an alcohol (C). Oxidation of (C) with
chromic acid produced (B). (C) on dehydration gives but-1-ene.Write equations for the
reactions involved.

14. An organic compound with molecular formula C7H7NO2 exists in three isomeric forms,
the isomer ‘A’ has the highest melting point of the three. ‘A’ on reduction gives
compound ‘B’ with molecular formula C7H9N. ‘B’ on treatment with NaNO2/HCl at 0-5
0C to form compound ‘C’. On treating C with H3PO2 ,it gets converted to D with
formula C7H8 , which on further reaction with CrO2Cl2 followed by hydrolysis forms
‘E’ C7H6O . Write the structure of compounds A to E . Write the chemical equations
involved.

15. An organic compound (A) with molecular formula C8H8O forms an orange-red precipitate
with 2,4-DNP reagent and gives yellow precipitate on heating with iodine in the presence
of sodium hydroxide. It neither reduces Tollens’ or Fehlings’ reagent, nor does it de
colourise bromine water or Baeyer’s reagent. On drastic oxidation with chromic acid, it
gives a carboxylic acid (B) having molecular formula C7H6O2. Identify the compounds
(A) and (B) and explain the reactions involved.

16. An organic compound (A) (molecular formula C8H16O2) was hydrolysed with dilute
sulphuric acid to give a carboxylic acid (B} and an alcohol (C). Oxidation of (C) with
chromic acid produced (B). (Q on dehydration gives but-l-ene. Write equations for the
reactions involved.
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